


He's My Cherry Pie

by phoenixserpens



Category: Supernatural
Genre: Anal Sex, Blow Jobs, Cherry pie by warrant, Deepthroating, Inspired by Music, M/M, Sam strips for Dean, Stripping
Language: English
Status: Completed
Published: 2019-11-19
Updated: 2019-11-19
Packaged: 2021-02-13 02:53:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,784
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21487144
Author URL: https://archiveofourown.org/users/phoenixserpens/pseuds/phoenixserpens
Summary: One day, Dean starts singing in the bunker. Sam notices, and keeps the song in mind. After a hunt pisses Dean off, Sam decides to surprise Dean with a strip show.
Relationships: Dean Winchester/Sam Winchester
Comments: 2
Kudos: 69





	He's My Cherry Pie

“_ She’s my cherry pie, _

_ Cool drink of water, _

_ Such a sweet surprise, _

_ Tastes so good _

_ Make a grown man cry, _

_ Sweet cherry pie…..” _

Sam blinked. Dean was singing in the bunker. On a normal Tuesday. They hadn’t been out of the bunker for the past couple of days, so chances were that Dean _ wasn’t _ cursed. Of course, knowing the Winchester Luck, he might have been.

Oh well. It wasn’t hurting anyone, and Dean had a nice voice. The way his voice could go all deep and husky, but be high and light for the next sentence killed Sam. When they had sex, Sam had a thing for Dean’s dirty talk. Not that Sam didn’t mind some of his own, but something about Dean’s low voice taunting him, looking up at him while sucking his cock, pulling off to say how he loved how Sam tasted, or how he wanted Sam to fuck his throat.

Sam shifted in his chair, his pants tight over his erection. He loved to facefuck Dean. Dean’s face was just so expressive, his lips perfect for sucking cock, and he got off on how Sam used his throat, which was incredibly hot. And because he was Dean, he couldn’t do anything sex-related halfway. No, Sam mused, of course Dean would be the one to practice deepthroating for hours until he could get Sam’s cock down his throat in one go. He knew just when to swallow, hollow his cheeks, or swirl his tongue around the head of Sam’s cock.

The best thing was how Dean sounded after he let Sam facefuck him. His voice went lower than it would usually, all hoarse and scratchy, but he would be as hard as a rock from being used, which suited Sam just fine.

Sam shut his laptop. He was done researching for now, distracted since Dean had started singing. He made a note to look up the song later, and some other classic rock as well. He had a few ideas for what he could do with this song. He decided to go find Dean.

Walking through the bunker, Sam found Dean in his room, cleaning his gun. He walked over to Dean’s bed and sat down next to Dean, too close to be anything but an invitation.

Dean smirked to himself. He had a feeling that Sam would be intrigued by the singing. The fact that Sam already had a boner was a plus.

“Well Sammy, I’d ask what you’re doing in here, but I think I can see why.” He looked Sam in the eye and grinned, seeing his brother relax, but a spark of heat flash in his eyes.

“Hmmm,” Sam said. “I don’t quite know what you mean.”

Fuck yeah, Dean thought. So this was how Sammy wanted to be today. He finished cleaning his Colt and stood up from the bed, walking over to put it on his dresser before walking back over to Sam and sinking to his knees between Sam’s legs. He watched Sam’s throat convulse as he swallowed.

Dean wasn’t always submissive when he and Sam fucked, they switched off. Sometimes it was nice to be in control of another person, or to be controlled. Other times they would fuck as equals, biting and marking each other as hard as they could. For blowjobs though, there was nothing better for Dean than making Sam come down his throat.

Dean unbuttoned Sam’s jeans and reached into his boxers to pull out his cock. Sammy’s cock was fucking delicious. Sam was long and thick, _ just like the rest of him _, Dean thought. He looked up at Sam, opened his mouth, and sank down onto Sam’s cock.

Sam moaned. Dean’s mouth was sin, hot and soft, squeezing his dick just right. He knew all of the tricks in the book, picked up by practical experience or from what he knew felt good to him, which luckily felt good to Sam too. Before they started getting each other off and fucking, Dean’s constant parade of conquests pissed Sam off, but now he couldn’t be more grateful as Dean sucked the head of his cock, using his right hand to jerk the part of Sam’s cock that wasn’t in his mouth, holding Sam’s hips down with the other.

“God, _ fuck _ Dean,” Sam breathed. Dean smirked around Sam’s cock, hollowing his cheeks and shaking with a bit of laughter when Sam fully flopped down backwards on the bed, losing the ability to hold himself up.

Dean kept going for another couple of minutes, Sam’s pants and moans making the whole thing hotter. Sam started thrusting his hips up more and more, almost breaking Dean’s hold and making him gag a few times, all part of what Dean loved though. It was time to make this better. Dean felt himself growing hard, he really did love to give Sam blowjobs. For now, it was time for Sam to do what he wanted.

He pulled off of Sam’s cock with a pop, sucking at the head just to see Sam’s hips jerk up. Sam twitched, taking a second to sit up properly while Dean composed himself. Dean sat back on his heels, looking up at Sam, his lips swollen and shiny.

“The usual, Sammy?” Dean asked, his voice hoarse. Sam shuddered and nodded. 

“Tap my thigh if it gets too much, I’ll warn you when I’m going to come.”

“Alright.” Dean took a breath in, getting some oxygen into his lungs before Sam lunged at him.

Sam wound his hands into Dean’s hair, as short as it was he could still get a grip, and hauled Dean forward onto his cock.

Dean gagged immediately, eyes tearing up, feeling Sam go down his throat. Sam held him there for a few seconds, long enough for Dean to recognize the feeling of not getting air into his lungs before drawing back and thrusting back in, picking up his pace. For his part, Dean grabbed onto Sam’s thighs and relaxed his throat, going pliant in Sammy’s hands.

Sam cursed. Dean was so pretty like this, mouth stretched over his cock and looking up at him with tears in his eyes. He sped up, his eyes closing at a particularly tight squeeze of Dean’s throat. He felt his hips stutter, he was close.

“Dean,” he choked out. “I’m going to -” He was cut off by an involuntary whine when Dean started fully sucking on him again _ while _ Sam facefucked him.

“Dean,” he tried again, “gonna come.” He opened his eyes to look at Dean’s face. Dean looked up at Sam, deliberately taking a long blink. It was their nonverbal signal for everything being okay.

Sam groaned, grabbing Dean and pulling him to the base of his cock, and came down his throat. Dean couldn’t breathe but he loved it, feeling Sammy twitch as he came. Sam drew back when he was done, and Dean wiped his mouth and sat back on his heels.

“How was that?” He asked, knowing full well how the grit of his voice turned Sam on.

Sam sat down heavily on the bed after tucking his cock away. “Good, so good, God Dean, that was one of the best you’ve ever given.” He flopped down on the bed again, but was interrupted by feeling Dean climb onto the bed, and onto him.

Dean smiled. “I’m glad, Sammy,” he trailed off. “Now, how about you repay the favor?”

Sam looked at Dean, a proud, dark feeling in his chest that he could get Dean hard by using him. He shrugged. “Why not?” He surged upward, and rolled Dean over on the bed so that he was above him. He looked down at Dean. With his lips still swollen and a little teary, Dean never looked so good.

He leaned down and kissed at Dean’s neck before nipping him and sucking a little around the bite to get a hickey on him. Sam loved marking Dean up, repeating his actions on the other side of Dean’s neck. He sat up and pulled off his own shirt, and reached at Dean to pull his off too.

He leaned back over Dean and starting biting and sucking marks down Dean’s chest, making sure to pluck at Dean’s nipples a bit.

Dean writhed a little beneath Sam, worked up from giving the blowjob. “Sammy, please,” he begged. “Don’t tease.”

Sam nodded, moving down to Dean’s jeans before opening them. Dean’s cock sprang out, he had gone commando that morning. The friction must have been killing him.

He took Dean’s head into his mouth, then slid down as far as he could before coming back up. Dean’s head thunked backwards onto the pillow where he had been looking at Sam.

Sam repeated his movements before pulling off and licking around where he couldn’t reach, getting Dean nice and slippery. He went back onto the first couple of inches of Dean’s cock before wrapping his hand around the rest of him, jerking him off quickly. Dean’s hands wound into Sam’s hair, not pushing him but to have something to grab onto.

Sam continued jerking Dean off while sucking him, knowing that Dean would hate to be denied. He felt Dean start to stiffen before Dean gasped out, “Gonna come, Sammy.” Sam kept sucking on Dean, and sank down a few extra inches.

Dean shook and his hips jerked up as he came, sliding down Sam’s throat, who choked but kept himself there while Dean came. He swallowed and cleaned Dean off before lying on the bed next to Dean, leaning over to kiss him.

A few weeks later, they had a rough hunt. A wendigo had been causing some problems up in South Dakota. Everything had been routine, but at the end of their fight with the wendigo, it hit Sam in the head when Dean missed a swing he had taken at its shoulder.

Sam was fine, but Dean was pissed at himself. He didn’t want to be the cause of more head trauma to his younger brother. They drove back to the bunker quickly, Dean blasting classic rock all the while, breaking a few speed limits on the way. When they got to the bunker, Sam and Dean went to stow away their gear, having showered and slept in the motel before they drove back. They didn’t speak much, and once everything was taken care of, Dean went to his room to sulk, and Sam went to his room to plan.

Sam wasn’t an idiot. He saw how angry Dean was, but when he tried to confront him and prove that he was okay, Dean just grunted, “I’m fine, Sam,” and they left it at that. Well, Dean left it.

A couple of days after the singing, Sam had looked up the song. The lyrics were about pie, but it was very clearly about sex, right up Dean’s alley. Sam listened to the song on repeat a few times, and could appreciate what Dean liked about it. Which brought him to his plan.

Dean was in a shitty mood, and usually only time would make him feel better, but Sam didn’t want to deal with a pissed off Dean for the next week or two. After listening to the song, he left the bunker to go on a grocery run, but stopped by a clothing store on his way. He decided to buy a pair of gray sweatpants, a cowboy hat, and a tight red shirt that looked like it was spray painted on him when he looked in the mirror. He had immediately blushed and gone to put it away, but reconsidered when he thought about how good he looked.

Sam pulled up a loop of “Cherry Pie” on his phone, intending for it to play as long as he wanted. He showered quickly and put on the sweatpants, shirt, and hat, looked in the mirror, cringed, and looked away. Then he looked back, and had to hand it to himself. He looked damn fine. The shirt was tight over his muscles, and the sweatpants weren’t going to do anything to conceal a boner, which would probably show up immediately. The hat was nice, but it was more for Dean’s enjoyment than Sam’s.

Sam took a deep breath to psych himself up. It was time for him to go seduce Dean.

Sam walked down the hallway, barefoot. He got to Dean’s room and tried to open the door. It was locked.

“Dean?” He asked.

“What is it, Sam? Anything weird going on? A new case?” Dean sounded annoyed.

“Nope. I just wanted to come talk.” Sam bit his lip. He wasn’t sure how to go about this, but he kept going. “You alright?”

Dean snorted. Sam could hear it through the door. “Just peachy. And we already talked, I’m fine. Now, can a man get some peace around here?”

Sam sighed. Good thing he brought the lockpicks.

“Hey! Sam! What’re you doing?” Dean heard Sam picking the lock. He got off the bed and unlocked the door, opened it, and came crotch to face with Sam kneeling on the ground.

Sam looked up at him, and Dean felt his blood to travel southward. He stepped back into the room, and Sam slowly stood up. He walked into the room, crowding Dean backward until Dean was standing against the bed.

“Dean, I don’t want to talk about today. It doesn’t matter,” Sam said. He kissed Dean, hard and fast until Dean was breathing heavily. “For now, just, sit and watch, alright?” Sam pushed Dean onto the bed so he was sitting and had a clear view of the room. Sam backed up a few feet, and put his phone onto Dean’s dresser. He pressed play on the loop and went to stand into the center of the room.

Dean looked confused, but as the song started to play his eyes sharpened, and he leaned forward to see what Sam was going to do.

“_ Dirty, filthy, rotten, stinkin’! _”

Sam started swaying his hips and walked towards Dean, trailing his hand down his torso.

“_ She’s my cherry pie, _

_ Cool drink of water, _

_ Such a sweet surprise, _

_ Tastes so good _

_ Make a grown man cry, _

_ Sweet cherry pie, yeah!” _

He reached Dean and pushed his legs apart, leaning into him and kissing at his neck. Dean reached for him, but Sam nimbly stepped away.

“Sammy!” Dean breathed.

“Stay where you are, Dean.” Sam ordered. Dean gulped and nodded.

“_ Well, swingin’ on the front porch, _

_ Swingin’ on the lawn, _

_ Swingin’ where we want _

_ ‘Cause there ain’t nobody home,” _

Sam traced his hands along his thighs before cupping his boner through his sweatpants. He had been right, the sweatpants hid nothing. He reached up and took off the hat, tossing it to Dean, who put it on.

_ “Swingin’ to the left _

_ And swingin’ to the right, _

_ If I think about baseball _

_ I’ll swing all night, yeah!” _

Sam lifted up the waist of his shirt, peeling it upwards to flash his abs, before dropping it back down. He trailed his hand over his chest, then up to his face where he teased his lips before sucking his index finger into his mouth. He slid the finger down his neck to his chest and then the waistband.

_ “Yeah, yeah! _

_ Swingin’ in the living room, _

_ Swingin’ in the kitchen, most folks don’t _

_ ‘Cause they’re too busy bitchin’ _

_ Swingin’ in there _

_ ‘Cause she wanted me to feed her, _

_ So I mixed up the batter, _

_ And she licked the beater” _

He pulled the shirt up slowly, teasingly. He pulled it over his head and tossed it into the corner of the room. He walked forward again, leaning into Dean and straddling his legs. He gave Dean a filthy kiss, drawing a moan from his brother. Again, just as Dean was getting into it, Sam backed off. To his credit, Dean stayed where he was, pupils blown and his lips swollen.

_ “I scream, you scream _

_ We all scream for her _

_ Don’t even try _

_ ‘Cause you can’t ignore her” _

Sam walked back a couple of feet, enough so that he had enough room. He turned around and bent over, grasped the waistband of the sweatpants and slowly worked them down, stepping out of them and kicking them to the side.

“_ She’s my cherry pie, _

_ Cool drink of water, _

_ Such a sweet surprise, _

_ Tastes so good _

_ Make a grown man cry, oh yeah!” _

He turned around, clad only in his boxers. Dean had a prominent bulge in his jeans now, his cheeks were flushed and his eyes were glazed, locked onto Sam.

_ “She’s my cherry pie, _

_ Put a smile on your face, _

_ Ten miles wide _

_ Looks so good, _

_ Bring a tear to your eye, _

_ Sweet cherry pie, yeah!” _

Sam walked back over to Dean, still swaying his hips. He reached for the waist of Dean’s shirt and pulled it off over his head, knocking the hat away. He unbuttoned Dean’s jeans and brushed the edge of his hand against Dean’s erection, dodging out of Dean’s attempt to grab him.

_ “Swingin' to the drums, _

_Swingin' to guitar _

_ Swingin' to the bass _

_ In the back of my car _

_ Ain't got money, _

_ Ain't got no gas _

_ But we'll get where we're goin' _

_ If we swing real fast” _

Dean slid out of his jeans, throwing them into the corner, keeping his eyes on Sam. Sam had paused just out of Dean’s reach, idly palming his cock through his boxers, his head thrown back and eyes closed.

_ “I scream, you scream _

_ We all scream for her _

_ Don’t even try _

_ ‘Cause you can’t ignore her” _

Sam opened his eyes, smirking at Dean. He toyed with the elastic of his boxers before sliding them down his hips. He paused for a second, hearing Dean groan. He pulled them down the rest of the way and kicked them into another corner, maybe under the bed. He didn’t care.

“_ She’s my cherry pie, _

_ Cool drink of water, _

_ Such a sweet surprise, _

_ Tastes so good _

_ Make a grown man cry, oh yeah!” _

He closed the space to Dean and kissed him again, trailing his hands down Dean’s sides to the waistband of his boxers, tugging at them to say that he wanted them off. He gave a quick bite to the side of Dean’s neck, and stepped back again. Dean yanked his boxers off, and sat waiting for Sam.

_ “She’s my cherry pie, _

_ Put a smile on your face, _

_ Ten miles wide _

_ Looks so good, _

_ Bring a tear to your eye, _

_ Sweet cherry pie, yeah!” _

Dean was shaking with the effort of holding himself back. He was tensed, eyes dark and hungry. Sam closed the space between them one final time and pushed Dean backwards on the bed, landing on top of him.

_ “Piiiieee, yeah! _

_ Yeah, swing it _

_ All night long, _

_ Swing it!” _

He kissed Dean, who wound a hand into Sam’s hair, pulling Sam closer to him. When they needed air he dipped his head onto Sam’s neck, leaving him a hickey in return for earlier.

_ “Like a trained professional! _

_ Swingin’ in the bathroom, _

_ Swingin’ on the floor _

_ Swingin’ so hard _

_ We forgot to lock the door” _

Sam ground his hips down into Dean’s, their cocks sliding together. Dean moaned, pulling Sam’s hair as he thrust his hips upwards for more friction. He guided Sam’s face back to his, bringing him in for another kiss.

_ “In walks her daddy _

_ Standin’ six foot four, _

_ He said, _

_ “You ain’t gonna swing with my daughter no more”” _

He blindly reached out for the side table on the bed, opening the drawer and pulling out the condoms and lube. He needed to fuck Sam, now.

“_ She’s my cherry pie, _

_ Cool drink of water, _

_ Such a sweet surprise, _

_ Tastes so good _

_ Make a grown man cry, oh yeah!” _

Sam sat up, bringing Dean with him. He wrapped a hand around their cocks and started jerking them together while they kissed again.

_ “She’s my cherry pie, _

_ Put a smile on your face, _

_ Ten miles wide _

_ Looks so good, _

_ Bring a tear to your eye, _

_ Sweet cherry pie! _

_ Sweet cherry pie, yeah! _

_ Swing it!” _

The song finished and started to play over again. “Sammy, please,” Dean gasped out. “I need to fuck you, now. I gotta open you up.”

Sam nodded and blushed. “I showered earlier, and I, uh, might have helped with that.”

Dean felt his heart stop for a second, imagining Sam in the shower fingering himself. He coated his fingers and cock in lube and worked a couple of fingers into Sam. He scissored his fingers trying to open Sam up but not hurt him. Sam jolted as Dean caught his prostate, clenching around Dean’s fingers. Dean worked in another finger, Sam had done well while showering. He kissed Sam, distracting him from the stretch and slowing himself down.

“You ready, Sammy?” Dean growled. His voice had gone deep with arousal, and Sam shivered.

“Yes, oh god, so ready Dean, please,” he begged.

Dean quickly opened a condom and rolled it onto himself, then lifted Sam up and lined him up with his cock, and Sam sank down slowly. He moaned at the feeling of being stretched open, while Dean clenched his hand around the bedsheets, supporting Sam’s thigh with the other.

Neither of them were going to last long, and Sam let out a keen as Dean filled him. He stayed still for a few seconds before adjusting and lifting himself back up, and slid back down. He picked up speed and began to ride Dean. Dean started slowly thrusting up into Sam, matching Sam’s movements. They both picked up speed until Sam was bouncing on Dean’s cock, jerking off his own.

“Dean,” Sam warned. “I’m going to come.” Dean moaned and started thrusting faster, moving his hand from the sheets onto Sam’s cock and began to jerk him off as well.

Sam’s thighs started to shake, but when he shifted his hips, Dean struck his prostate dead on. He screamed and came, clenching around Dean. Dean gave a roar and came a few thrusts later, his vision whiting out.

When they came back down from their highs, Dean took off the condom and chucked it into the trash. He kissed Sam, and smiled against his lips before looking at him.

“You are gorgeous, you know that, right?” Dean asked.

Sam grinned. “I figured it out pretty fast.” He cuddled up to Dean and laid his head on his chest.

“Time for a nap,” he yawned. Dean laughed.

“Sure thing, Sammy.” He wrapped his arms around Sam, and they fell asleep with the song still playing in the background.

_ “Looks so good _

_ Bring a tear to your eye, _

_ Sweet cherry pie, yeah!” _

**Author's Note:**

> I was listening to some classic rock and listened to this song again, and I remembered how much Dean likes pie. And Sam. And sex. This was the result.  
Also, I don't own the song Cherry Pie by Warrant, or Supernatural.  
I hope you like it, let me know how it is! :)


End file.
